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Sebago Dan — Men's Penny Loafer Moccasins in Brown Leather -
Dan Lug Black Leather Loafers with Tank Sole -
Sebago Dan Neri Leather Loafers – Classic Penny Loafer -
Men's Hammered Leather Penny Loafers – Elegant Made in Italy -
Classic Dan Woman - Full Grain Leather Penny Loafer -
Men's dark brown suede penny loafers -
Barrett Polished Dark Brown Leather Loafers
The penny loafer is the loafer with a leather strap across the vamp, featuring a central slit. The name comes from American students in the 1950s, who slipped a one-penny coin into the slit so they would always have the money for a phone call. It remains the most understated loafer there is, which is why it never goes out of style.
The beefroll: the detail to look for
On a well-made penny loafer, the strap is not simply stitched on top: both sides are rolled and reinforced, forming two small ridges at the ends. This is called beefroll construction, and you will find it on the Sebago Dan, which are hand-stitched.
It is not merely an aesthetic detail: those ridges are where the shoe works hardest as the foot moves in and out, and reinforcing them is what keeps the strap in place for years. Looking at a photo, it is the quickest way to tell whether you are looking at a serious penny loafer or a shoe that only imitates its shape.
Doucal's, on the other hand, uses moccasin stitching with bag construction: the upper wraps around the foot without a rigid structure, making the shoe flexible from the first day.
Which one to choose
If you are looking for the archetypal penny loafer, choose the Sebago Dan: clean lines, leather, nothing superfluous. We stock it in black and brown, as well as the Dan Lug version with a lug sole, which is the same shoe made suitable for winter.
If you need a more elegant version, the Barrett styles have a stitched leather sole with an anti-slip insert and a slimmer profile: they work with a suit, where the Dan would be too casual.
In between is the Doucal's in pebbled leather, the choice for anyone who wants an Italian shoe without the austerity of a lace-up.
What to wear it with
The penny loafer is the most versatile of loafers precisely because it says nothing: it works with a suit, chinos or straight-leg jeans. It is the shoe you buy when you want just one pair.
The only combination that does not work is with trousers that are too short and colorful socks: the penny loafer is an understated model, and overloading it with signals distorts its character. If you want a loafer that makes a statement, look at the one with tassels.
Sizing and care
The selection runs from 36 to 45, with many half sizes. Fit is more critical in a penny loafer than in other models because the strap is the only element holding the foot in place: it should be snug without pressing on the instep.
Sebago leather moulds to the foot during the first few weeks and then retains its shape: if it is slightly snug at first, the fit is right. If it feels comfortable immediately, it will become loose with wear.
For care, apply neutral cream occasionally and use shoe trees while the shoes rest. With a leather sole, avoid heavy rain and let it air-dry, never near a radiator.
Where to look next
- Tassel loafers — the tassel loafer, more distinctive
- Men's loafers — every style
- Sebago — home of the Dan
- Men's shoes — the complete selection
Frequently asked questions
Why is it called a penny loafer?
In the 1950s, American students slipped a one-penny coin into the slit in the strap across the vamp: it was the cost of a call from a payphone, and keeping it there meant they could call home. The name remained even after the coin disappeared.
What is beefroll construction?
It is the way the sides of the strap are rolled and reinforced rather than simply stitched, forming two small ridges at the ends. It reinforces the point where the shoe works hardest and distinguishes a well-made penny loafer. In our selection, it is used on the Sebago Dan, which are hand-stitched.
Is a penny loafer or tassel loafer better?
It depends on how much you want the shoe to stand out. The penny loafer is understated, works with any trousers and imposes nothing on the rest of the outfit. The tassel loafer is a distinctive detail that draws attention. If you are buying just one pair, the penny loafer is the safest choice.
Should you wear it with or without socks?
In summer, you can wear invisible socks, in keeping with the tradition of the style. In winter, socks work well, provided they are understated and from the same color family as the trousers. Sporty white socks are the only thing that truly clashes.
Are there women's styles?
Yes. The Sebago Classic Dan is also available in a women's version, and we stock it in black, along with the Dan Lug with its lug sole. The selection starts at 36.